Alkylaminomethylpentyl benzoate.



THADDllUS EMILEWIOZ, OF BERLTN,

FABRlK AUF ACTIEN, VORM. E.

GERMANY. ASSIGNOR TO onsn'rsons SQHERINGJ BERLIN, GERMANY.

ALKYLAMINOM ETHYLPEN-TYL BENZOATE.

Specification of Letters Patent.

Patented Dec. 4, 1908.

Application on March 14,1906. Serial No. 306.043.

To all whom it may concern:

' .Be it known that I, THADDAUs E ILEWIGZ,

1 doctor of :philosophy, chemist, a subfiect of the Emperor ofAustria-Hungary, residing at Berlin, Kingdom of Prussia, German Einpire,have invented a new and useful improvement in the Manufacture ofAlkylaminomethylpentyl Benzoates, of which the following is aspecification.

The hitherto-unknown alkylaminomethylpentyl benzoates, which possessanesthetic properties, may be obtained by benzoylating'alkylaminomethylpentanols as such or in the form of their salts,-forexample, by treatment with anhydrous benzoic acid or benzoyl chlorid orlike benzoylating agents.

The alkylaminomethyl entyl benzoates correspond to'the general ormulacsr-c-cnr-on o-co-conr able in water and are distinguished by acompl'etelyineutral reaction even when highly concentrated.

E sample 1 Mefhylaminomethylygcmyl benzoate, (methyldiacetone (Ilka-minenscate.)Three hundred and fifty methylaminomethylpentanol(methyldiacetone alkainin; see M. Kohn, Monatshej'te fair C'hcm'ie,1904, age 137) are dissolved in one hundred and 'fi ity grams of warmwater and heated with six hundred grams of anhydrous benzoicacidf'or oneand one-half to two hours u on a waterbath. Hydrochloric acid is a dedto acidity, and the precipitated benzoic acid is removed by filtrationwith the aid of suction. The solution-of the product of the reactionismade alkaline with soda and extracted with ether. oilthe etherealsolution the free methylaminomethylpentyl benzoate remains behind asAfter distilling a heavy oil. The hydrochloric-acid salt crystallizesout of a mixture of alcohol and ether l'centigrade, (uncorrected) Tenparts of the hydrochloric-acid salt dissolve in thirteen parts of waterat 15 centigrade.

l Example th'ylaminomethylpentyl benl 'zoate, (ethyldia cetoneallcaminbenzoaie.)l.45

kilograms of yldiacetone l Ghe'mie, 1904, page 137) are dissolved in itgives a feeblyacid reaction. l then The other is water and for thepurpose of removing the benzoic acid and small quantities of impuri tiesis shaken with ether or benzene. The product is whitened by means ofanimal charcoal .and the compound set free with an alkali. The separatedfree ethylaminomethylpentyl' benzoate is a strongly basic oil. Thehydrochlorioacid salt crystallizes out of a mixture of alcohol and etherin microscopic small needles which combine to iiorm a conglomerate. Themelting-point lies at about 172 to 173centigrade, (inicorrectedl Example3Dimethylhmimmethyl entyl t benzoate, (dimethyldiacetonealkamin hemolate.)-1f in the foregoing exam le the lethylaminomethylpentanol(ethyldiacetone alkarnin) be replaced by dimethylaminomethylpentanol(dimethyldiacetone alkamin) i (lie-netshcftefi/Lr C7zem'ie,1904, page137) and l.the process be carried out as before, the di-v metiylaminoinethylpentyl benzoate is prol duced as a basic oil whosehydroch oric acid salt trickles at about 145 to rat" centigradeliuncorrected) and melts lit about 153". to

cules o1 ethyl iodid to react upon the aminomethyl pentanol(diethyldiacetone alkamin) in thin needles melting at about 151 to 162ethylaminomethylpentanol'(eth-' v alkamin see. lllonatshefte hreekilograms of ether, and hydrochloricacid gas is passed through thesolution until distilled off and the dried hydrochloric acid salt heatedwith 1.6 kilograms of ben-' 1 zoyl chlorid for three to four hours at130 to r a kamina) may 4 The die'thyleminomethylpentanol (diethn mayalso performed by using; other: elkyleting agents, such as salts ofethylsulfi1rreucid,in place of ethyl iodid or by treating 'themonoethylaminomethylpentanol (IDOIIO iethyldiacetone alkamin) with analkyleting a ent. n ln an analogous manner also the other dialklaminomethylpentanols (dialkyldiaoetone be produced.

yldiacetone alkemin) is a colorless oil boilmg at 204 to 206 centigrade(uncorrected) at ordinaryfpressure.

To obtain the benzoyl connound, eight hundred and-sixtg grams ofiethylaminomethylpentanol iethyldiacetone elkainin) are'dissolved in twohundred and fifty cubic centimeters ofi'benzene iend eight hundred andfifty'grams of benzoyl ohlorid are added thereto. The mixture is thenheated for one to two hours at 100 centigrade, then cooled and filteredby suction. 'lhe hydrochloricacid salt results, from which the base isset free. The {hydrochloric-acid salt crystallizes; y

from a mixture of acetone and ether in small needles melting at about121 to 122 centigrade, .(unorrected g In testimony whereof I Other elkylderivatives can 'be=formed in an analogousmanner.

I claim as my invention- I 30 I As new chemical products, theelkylaminomethylpentyl benzoates, the constitution pf whi c'h'answersthe formula' the free bases being oilIy bodies diifi'cultq solubleinwater, but easi y soluble in organic 4 i solvents, and. combiningwithinorganic and organic acids to form the correspondingsalts which haveanesthetic properties.

have hereunto semy hand this 23d day of Februar 1906.

THADDA'US EMI EWICZ.

Witnesses;

HENRY HASIER, WOLDEMAR HA'UPL'

